Coloration acid dyes

CHEMISTRY OF ANTHRAQUINONOID, POLYCYCLIC AND MISCELLANEOUS COLORANTS Acid dyes... 

Most xanthene dyes are classified as basic dyes by their method of appHcation acid dyes can be produced by introduction of sulfonic acid groups. The fluoresceins, which contain carboxy and hydroxy substituents, are also acid dyes for coloration of silk. Some of the fluoresceins in which the carboxy group has been esterified, are soluble in alcohol or other organic solvents and can be classified as solvent dyes. Mordant dyes can be produced by introducing o-dihydroxy or sahcyhc acid groups (2), which when metallised can have very good lightfastness. 

Chrome-tanned leather has chromium bonded to the leather fibers. This chromium can act as a mordant for acid dyes resulting in fast colors and intense shading at the surface of the leather. 

Dyes. Sodium nitrite is a convenient source of nitrous acid in the nitrosation and diatozation of aromatic amines. When primary aromatic amines react with nitrous acid, the intermediate diamine salts are produced which, on coupling to amines, phenols, naphthols, and other compounds, form the important azo dyes (qv). The color center of the dye or pigment is the -N=N- group and attached groups modify the color. Many dyes and pigments (qv) have been manufactured with shades of the entire color spectmm. 

Mordant Dyes. MetaUizable azo dyes are appHed to wool by the method used for acid dyes and then treated with metal salts such as sodium chromate [7775-11-5] sodium dichromate [10588-01-9] and chromium fluoride [1488-42-5] to form the metal complex in situ. This treatment usually produces a bathochromic shift ia shade, decreases the solubUity of the coloring matter, and yields dyeiags with improved fastness properties. The chromium salts can be appHed to the substrate before dyeiag (chrome-mordant or chrome-bottom method), together with the dye ia a single bath procedure (metachrome process), or as a treatment after dyeiag (afterchrome process). 

Barium chloride finds use in the production of barium colors, such as the diazo dyes barium hthol ted [50867-36-2] and barium salt of Red Lake C [5160-02-1], a mordant for acid dyes and dying of textiles. Other uses include aluminum refining and boiler water treatment. 

U-in alkaline-reducing vats, a soluble leuco compound forms I-insoluble J-tends to thicken or gel the solution p-dye precipitated as heavy-metal salt or color acid a-may bleed or stain, very sparingly soluble S-dissolves (solubiUty 1%). 

Some 50% of all nylon is in the form of carpets almost exlusively colored with acid dyes, and around 50% of the carpet manufacturing industry is located in the United States. The acid dyes from Group 1 are those most widely used because they exhibit the rapid diffusion needed to penetrate the bulky yams used in carpets, especially bulk continuous filament yam used in tufted constmctions, with high exhaustion. Their wetfastness properties are generally adequate for most oudets. 

Acetate fibers are dyed usually with disperse dyes specially synthesized for these fibers. They tend to have lower molecular size (low and medium energy dyes) and contain polar groups presumably to enhance the forces of attraction by hydrogen bonding with the numerous potential sites in the cellulose acetate polymer (see Fibers cellulose esters). Other dyes can be appHed to acetates such as acid dyes with selected solvents, and azoic or ingrain dyes can be apphed especially for black colorants. However thek use is very limited. 

Wool—Acrylic Fibers. This blend is being used for iadustrial and hand knitting yams. The acryHc fiber is aesthetically similar to wool, iacreases the strength of the yam, and adds bulk to the goods. Special precautions are necessary siace the two fibers are colored with dyes of opposite ionic type. Coprecipitation is prevented with the use of an antiprecipitant. Usually, level dyeing acid dyes are used for the wool portion in combination with the cationic dyes for acryHc fiber. 

In this work hybrid method is suggested to determine cationic surfactants in water. It is based on preconcentration of cationic surfactants in the some of ion associates with acidic dyes on the paper filter and measurement of color intensity by solid-phase specdophotomenic method or visual comparison. 

Acid dyes used for coloring animal fibers via acidified solution (containing sulfuric acid, acetic acid, sodium sulfate, and surfactants) in combination with amphoteric protein. 

Arylamines are converted by diazotization with nitrous acid into arenediazonium salts, ArN2+ X-. The diazonio group can then be replaced by many other substituents in the Sandmeyer reaction to give a wide variety of substituted aromatic compounds. Aryl chlorides, bromides, iodides, and nitriles can be prepared from arenediazonium salts, as can arenes and phenols. In addition to their reactivity toward substitution reactions, diazonium salts undergo coupling with phenols and arylamines to give brightly colored azo dyes. 

Phenols (capable of coupling) Fast blue salt B, fast blue salt BB, fast black salt K, diazotized sulfanilic acid (Pauly s reagent) diazotized sulfanilamide or 4-nitroaniline Intensely colored azo dyes are formed. Catecholamines [20, 3S], imidazoles [21] and amines capable of coupling also react. [3, 17]... 

Primary alcohols can be selectively detected using reagent sequences involving an initial oxidation to yield aldehydes that are then reacted in acid medium with electron-rich aromatics or heteroaromatics, according to the above scheme, to yield intensely colored triphenylmethane dyes. 

Classical examples of this type of reaction are the various dimethylaminobenz-aldehyde reagents (q.v.) and vanillin-acid reagents, of which one, the vanillin-phosphoric acid reagent, is already included in Volume 1 a. The aldol condensation of estrogens is an example for the reaction mechanism (cf. Chapter 2, Table 6). According to Maiowan indole derivatives react in a similar manner [1]. Longo has postulated that catechins yield intensely colored triphenylmethane dyes [2]. 

The general aspects of the aldehyde-acid reaction were discussed in Chapter 2. Thus it is readily understood that catechins, for example, can react with aromatic aldehydes in the presence of strong acids to yield colored triphenylmethane dyes [26]. 

The traditional use of dyes is in the coloration of textiles, a topic covered in considerable depth in Chapters 7 and 8. Dyes are almost invariably applied to the textile materials from an aqueous medium, so that they are generally required to dissolve in water. Frequently, as is the case for example with acid dyes, direct dyes, cationic dyes and reactive dyes, they dissolve completely and very readily in water. This is not true, however, of every application class of textile dye. Disperse dyes for polyester fibres, for example, are only sparingly soluble in water and are applied as a fine aqueous dispersion. Vat dyes, an important application class of dyes for cellulosic fibres, are completely insoluble materials but they are converted by a chemical reduction process into a water-soluble form that may then be applied to the fibre. There is also a wide range of non-textile applications of dyes, many of which have emerged in recent years as a result of developments in the electronic and reprographic... 

There is a wide diversity of chemical structures of anthraquinone colorants. Many anthraquinone dyes are found in nature, perhaps the best known being alizarin, 1,2-dihydroxyanthraquinone, the principal constituent of madder (see Chapter 1). These natural anthraquinone dyes are no longer of significant commercial importance. Many of the current commercial range of synthetic anthraquinone dyes are simply substituted derivatives of the anthraquinone system. For example, a number of the most important red and blue disperse dyes for application to polyester fibres are simple non-ionic anthraquinone molecules, containing substituents such as amino, hydroxy and methoxy, and a number of sul-fonated derivatives are commonly used as acid dyes for wool. 

The great majority of coloration processes demand some control over the treatment pH, which varies from strongly alkaline in the case of vat, sulphur or reactive dyes, to strongly acidic for levelling acid dyes. The concept of pH is a familiar one its theoretical derivation can be found in all standard physical chemistry textbooks and has been particularly well explained in relation to coloration processes [6,7] both in theory and in practice. We are concerned here essentially with the chemistry of the products used to control pH and their mode of action. It has been stated [7] that Unfortunately, pH control appears simple and easy to carry out. Add acid and the pH decreases add base (alkali) and the pH increases. However, pH is the most difficult control feature in any industry . 

Nitro dyes exhibit benzenoid-quinonoid tautomerism (1.25) and their colour is attributed mainly to the o-quinonoid form, since this can be stabilised by hydrogen bonding. The tautomeric o-nitrosonaphthols (1.26) readily form chelate complexes with metals. A few yellow nitro disperse dyes, including Cl Disperse Yellow 1 (1.25), and brown acid dyes remain of significance. The remaining nitro and nitroso colorants, such as (1.26) and its 1 3 iron (II) complex (1.27), are no longer of commercial interest. 

The first acid dye, Orange I (1.53 Cl Acid Orange 20), was discovered in 1876. All but a handful of the acid dyes developed since then were evaluated initially with wool dyeing in mind. In terms of adaptability to the coloration of other substrates, however, acid dyes have proved pre-eminent. This is the main reason for their number and variety. As well as the dyeing and printing of nylon and protein fibres, acid dyes are important for the coloration of leather, paper, jute, wood and anodised aluminium. Most of the permitted dyes for food and... 

There is as yet no agreed international list of permitted food colours. Thus a food dye that is permitted in one country may be considered unacceptable in another. The synthetic food colorants permitted in the European Union are listed in Table 1.8 [60]. All were originally introduced as acid dyes for wool many years ago. Furthermore, more than thirty colorants of natural origin are permitted in most countries. The natural carotenoid dyes are of outstanding importance for colouring edible fats and oils. These yellow to red methine dye structures occur in many families of plants and animals, including vegetables, berries,... 

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